New Chiral Zwitterionic Phosphorus Heterocycles: Synthesis,Structure, Properties and Application as Chiral Solvating Agents |
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| Authors: | Dr Andrey E Sheshenev Dr Ekaterina V Boltukhina Anastasiya A Grishina Dr Ivana Cisa?ova Dr Ilya M Lyapkalo Dr King Kuok Hii |
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| Institution: | 1. Department of Chemistry, Imperial College London, Exhibition Road, SW7 2AZ London (UK), Fax: (+44)?2075945804;2. Institute of Organic Chemistry and Biochemistry AS CR, v.v.i. Flemingovo nam. 2, 166 10 Prague 6 (Czech Republic);3. Department of Inorganic Chemistry, Charles University, Hlavova 2030, 12840 Prague 2 (Czech Republic) |
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| Abstract: | A family of new chiral zwitterionic phosphorus‐containing heterocycles (zPHC) have been derived from methylene‐bridged bis(imidazolines). These structures were unambiguously determined, including single‐crystal XRD analysis for two compounds. The stability, acid/base and electronic properties of these dipolar phosphorus heterocycles were subsequently investigated. zPHCs can be successfully employed as a new class of chiral solvating agents for the enantiodifferentiation of chiral carboxylic and sulfonic acids by NMR spectroscopy. The stoichiometry and binding constants for the donor–acceptor complexes formed were established by NMR titration methods. |
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| Keywords: | binding constants chirality enantioselectivity NMR spectroscopy phosphorus heterocycles zwitterions |
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